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Mandy Moore was just 15 years old when she released her first pop single ‘Candy’ in 1999. Twenty-one years later and we have to admit, she’s still like sugar to our heart. Just like her musical style, Moore’s sartorial choices have evolved over the years from the typical pop star uniform (think: low-rise jeans with blazers or flowy tops) to a more sophisticated penchant for elevated and tailored basics. Of course, more recently she couldn’t help but add a dose of Rebecca Pearson-inspired ‘70s style to her repertoire, but we’re getting ahead of ourself. Now, let’s take a little trip down memory lane to see just how the 36-year-old performer’s style has transformed over the years.

RELATED: Watch Mandy Moore Transform Into 80-Year-Old Rebecca for ‘This Is Us’

mandy moore performing in 1999
KMazur/Getty Images

1999: Hitting the Charts

We’re fairly certain every teen from this era also owned a ruffle-hemmed butterfly top (probably from Delia*s) and low-rise baby pink trousers (probably from Express).

mandy moore in 1999
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1999: Bubblegum Pink

The bright pink top and vibrant plaid skirt only seem to amplify Moore’s bubbly smile.

mandy moore at the 2000 peoples choice awards
Jeff Kravitz/Getty Images

2000: A Metallic Twinged Suit

Honestly, we could see someone wearing something very similar to this very look—a feminine suit and strappy square-toe sandals—today and not look out of place. Bravo on the timeless outfit, Mandy.

mandy moore in 2000
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2000: High-Low Mix

Party up top, casual denim down below. This is another combo we’d consider copying for the holidays, although we’d definitely pick different silhouettes (let’s hope handkerchief hem denim skirts never make a comeback).

mandy moore and ann hathaway in 2001
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2001: Moore’s Acting Debut

OK, so the pop star’s first acting gig was actually a voiceover for Dr. Dolittle 2 with Eddie Murphy. But who could ever forget her turn as Lana Thomas, popular cheerleader and enemy to the one and only Princess Mia Thermopolis. Unfortunately for Moore, we’d say Hathaway’s strapless dress was probably more movie premiere appropriate than her super light-wash jeans and platform loafers.

mandy moore at the 2002 premiere of a walk to remember
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2002: A Walk (and Belt) to Remember

The early 2000’s were a confusing time in fashion for just about everyone. For instance, we all thought cinching a billowing mini dress with a belt around our hips (rather than at the natural waist) was the most flattering way to go. What a time.

mandy moore in 2003
Jeff Kravitz/Getty Images

2003: The Uniform

This was a sort of red carpet uniform for stars of the early aughts—a flowy, semi-sheer top, low-rise bootcut jeans and super-strappy heeled mules.

mandy moore in 2005
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2005: Bermuda Shorts

Moore actually sported versions of this look—Bermuda shorts, platform sandals and a long-sleeve top—from 2004 through 2007, some better than others. But we actually kind of dig the neutral safari hues and easy proportions of this particular variation. No comment on the belt though…

mandy moore at the 2007 grammys
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2007: Boho Meets Rock

The flowy maxi! The wide studded belt! The towering wedge slingbacks! In terms of Grammy Award show ensembles, this is really very tame, but we appreciate Moore’s addition of that contrasting belt for an attempt at edge.

mandy moore in 2009
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2009: Studded Vest

Ah, 2009. The year when punk rock served to inspire the wardrobes of lots of celebs—Moore included. All she’s missing is a fringed scarf to go with her band tee, studded vest and dark wash skinny jeans.

mandy moore at the 2010 premiere of tangled
Craig Barritt/Getty Images

2010: Grown-Up Disney

After taking a break from music, Moore starred as everyone’s favorite frying pan-wielding princess in Disney’s Tangled with Zachary Levi. And while the bright magenta hue and full A-line skirt of this red-carpet mini certainly gives off some Rapunzel vibes, the one-shoulder neckline and architecturally draped bodice give it a more fashion-forward feel.

mandy moore in 2012
Stefanie Keenan/Getty Images

2012: Playing with Prints

We’re pretty sure 2012 was the height of the print mixing craze. But Moore’s pairing of black-and-white striped sandals with a geometric printed frock hits just the right level of interest, without feeling over the top.

mandy moore in 2013 at a topshop event
John Sciulli/Getty Images

2013: Simple and Stunning

This is around the time that Moore starts to embrace the power of perfectly tailored basics, with just a touch of something special (we’re looking at you, mod kitten-heel booties).

mandy moore in 2014
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2014: A Classic Mix

This is not the first time, nor will it be the last, that we found Moore draping her jacket elegantly over her shoulders like a cape. And that leather pencil skirt? We’re fans.

mandy moore in 2015
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2015: Breton Stripes

Another draped moment, this time over an adorable Parisian-inspired getup we’d gladly copy any day of the week.

mandy moore at the 2016 emmys
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2016: A ‘70s Influence

Oh, hello, Rebecca Pearson. All the gorgeous ‘70s-era costumes Moore wears to play the matriarch of the Pearson family in NBC’s This Is Us definitely inspired the actress to play with a mix of retro silhouettes, including this ruffled halter number.

mandy moore at the 2017 golden globes
Frazer Harrison/Getty Images

2017: A Caped Gown

Let the caping continue! Moore chose this gorgeous low-cut gown for the 2017 Golden Globes for which she was nominated for Best Supporting Actress in a Series, Miniseries or Television Film. (She, unfortunately, lost out to Olivia Colman for The Night Manager.)

mandy moore in 2017
Michael Koccisano/Getty Images

2017: Pretty in Plaid

Not quite as vibrant as her earlier pink-and-green plaid maxi skirt, this strapless midi feels infinitely more grown up, especially when paired with matching bright red pumps, a sleek updo and red lipstick.

mandy moore in 2018
Stefanie Keenan/Getty Images

2018: Lovely Leopard

What’s the easiest way to dress up a simple LBD? With a leopard print jacket and brightly hued strapped sandals, à la Moore at a fashion week party. (Of course, standing in front of a beautiful flower wall certainly won’t hurt.)

mandy moore in 2018 at paris fashion week
Pascal Le Segretain/Getty Images

2018: A New Favorite

Similar to her love of capes, Moore has developed a penchant for pairing bright pink with cherry red, a trend that started with this Schiaparelli stunner during Paris Fashion Week.

mandy moore recieving a star on the hollywood walk of fame in 2019
Kevin Winter/Getty Images

2019: A Hollywood Walk of Fame to Remember

Eight albums and more than 30 acting credits later, Moore finally received a star on the Hollywood Walk of Fame. What should one wear to such a momentous occasion? We think the superstar’s burgundy pumps and vaguely retro pleated frock were a classic and gorgeous choice.

mandy moore at the 2019 emmys
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2019: Pink and Red, Again

This is actually the third red carpet that saw Moore in this bold color combo, through this time she wasn’t the only one. In fact, at least four other attendees rocked pink and red to the Emmy’s that year.

mandy moore in 2020
Taylor Hill/Getty Images

2020: Red-Carpet Jumpsuit

A return to her signature style (aka, a cape), we love this retro-inspired jumpsuit and how the actress kept her hair, accessories and makeup simple to allow such an unexpected design to really shine.

2020: Baby’s First Award Show

Moore announced earlier this year that she and husband, Taylor Goldsmith, are pregnant with their first child. And while we’ve only been able to glimpse a peek of her pregnancy style here and there, we adore the simple elegance of this Brandon Maxwell column gown with those bold blue earrings.

RELATED: Wait, How Will ‘This Is Us’ Deal with Mandy Moore’s Pregnancy for the Upcoming Season?

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